1,2-Diaminocyclohexane, trans- → (5S)-1-{4-[3-(2-methylpyrrolidin-1-yl)propoxyl]phenyl}-5-(piperidin-1-ylmethyl)pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-[3-(4-iodophenoxy)propyl]-2-methylpyrrolidine a5 (0.245 g, 0.71 mmol, 1 eq) in dioxan (4 ml), potassium phosphate (0.3 g, 1.42 mmol, 2 eq), copper iodide (0.001 g, 0.007 mmol, 1 mol %), trans-1,2-diaminocyclohexane (0.008 g, 0.07 mmol, 10 mol %) and (5S)-5-(piperidin-1-ylmethyl)pyrrolidin-2-one a15 (0.155 g, 0.85 mmol, 1.2 eq) is placed in a sealed tube under argon atmosphere and heated at 110° C. until reaction completion. The mixture is diluted with dichloromethane and is washed twice with a solution of 1 M sodium hydroxide. The organic layer is dried over magnesium sulfate and concentrated in vacuo to give 279 mg of a brown oil. This oil is purified by chromatography on silicagel (dichloromethane/ethanol/ammonia 95/5/0.5) to afford 130 mg of (5S)-1-{4-[3-(2-methylpyrrolidin-1-yl)propoxyl]phenyl}-5-(piperidin-1-ylmethyl)pyrrolidin-2-one 48 as a pink oil.

Provenance & Evidence